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First reports: (a) Hoppe, I.; Hoppe, D.; Wolff, C.; Egert, E.; Herbst, R. Angew. Chem. Int. Ed. Engl. 1989, 28, 67. (b) Scolastico, C. Pure Appl. Chem. 1988, 60, 1689.
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0000545589
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First reports: (a) Hoppe, I.; Hoppe, D.; Wolff, C.; Egert, E.; Herbst, R. Angew. Chem. Int. Ed. Engl. 1989, 28, 67. (b) Scolastico, C. Pure Appl. Chem. 1988, 60, 1689.
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(a) Hoppe, I.; Hoppe, D.; Herbst-Irmer, R.; Egert, E. Tetrahedron Lett. 1990, 31, 6859.
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0001886121
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(d) Conde-Frieboes, K.; Harder, T.; Aulbert, D.; Strahringer, C.; Bolte, M.; Hoppe, D. Synlett 1993, 921.
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0028631014
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Prien, O.1
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Krettek, T.4
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Hoppe, D.8
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(h) Poli, G.; Maccagni, E.; Manzoni, L.; Pilati, T.; Scolastico, C. Synlett 1995, 71. Winter, E.; Hoppe, D. Tetrahedron 1998, 56, 10329.
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Poli, G.1
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Scolastico, C.5
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11
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(h) Poli, G.; Maccagni, E.; Manzoni, L.; Pilati, T.; Scolastico, C. Synlett 1995, 71. Winter, E.; Hoppe, D. Tetrahedron 1998, 56, 10329.
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Winter, E.1
Hoppe, D.2
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0028240876
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For similiar uses of N-Boc-1,3-oxazolidines see: (a) Agami, C.; Couty, F.; Lequesne, C. Tetrahedron Lett. 1994, 35, 3309. (b) Colombo, L.; Di Giacomo, M. Tetrahedron Lett. 1999, 40, 1977; and references cited therein.
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Agami, C.1
Couty, F.2
Lequesne, C.3
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13
-
-
0033525670
-
-
and references cited therein
-
For similiar uses of N-Boc-1,3-oxazolidines see: (a) Agami, C.; Couty, F.; Lequesne, C. Tetrahedron Lett. 1994, 35, 3309. (b) Colombo, L.; Di Giacomo, M. Tetrahedron Lett. 1999, 40, 1977; and references cited therein.
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Colombo, L.1
Di Giacomo, M.2
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0025730942
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Application of N-unsubstituted or alkyl-substituted 1,3-oxazolidines: (a) Ukaji, Y.; Yamamoto, K.; Fukui, M.; Fujisawa, T. Tetrahedron Lett. 1991, 32, 2919. (b) Mokhallalati, M. K.; Muralidharan, K. R.; Pridgen, L. N. Tetrahedron Lett. 1994, 35, 4267. (c) Kanemasa, S.; Suenaga, H.; Onimura, K. J. Org. Chem. 1994, 59, 6949.
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Ukaji, Y.1
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Fujisawa, T.4
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15
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0028238642
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Application of N-unsubstituted or alkyl-substituted 1,3-oxazolidines: (a) Ukaji, Y.; Yamamoto, K.; Fukui, M.; Fujisawa, T. Tetrahedron Lett. 1991, 32, 2919. (b) Mokhallalati, M. K.; Muralidharan, K. R.; Pridgen, L. N. Tetrahedron Lett. 1994, 35, 4267. (c) Kanemasa, S.; Suenaga, H.; Onimura, K. J. Org. Chem. 1994, 59, 6949.
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Mokhallalati, M.K.1
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Pridgen, L.N.3
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16
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0028114967
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Application of N-unsubstituted or alkyl-substituted 1,3-oxazolidines: (a) Ukaji, Y.; Yamamoto, K.; Fukui, M.; Fujisawa, T. Tetrahedron Lett. 1991, 32, 2919. (b) Mokhallalati, M. K.; Muralidharan, K. R.; Pridgen, L. N. Tetrahedron Lett. 1994, 35, 4267. (c) Kanemasa, S.; Suenaga, H.; Onimura, K. J. Org. Chem. 1994, 59, 6949.
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Kanemasa, S.1
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17
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0025992651
-
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For the use of chiral bicyclic 1,3-oxazolidines, see: (a) Review: Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503. (b) Leading reference to more recent work of A. I. Meyers et al.: Meyers, A. I.; Seefeld, M. A.; Lefker, B. A.; Blake, J. F.; Willard, P. G. J. Am. Chem. Soc. 1998, 120, 7429. (c) Review: Ager, D. J.; Prakash, I.; Schaad, D. Chem. Rev. 1996, 96, 835. (d) Leading reference to the work of H.-P. Husson et al.: François, D.; Lallemand, M.-C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. J. Org. Chem. 1997, 62, 8914.
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Romo, D.1
Meyers, A.I.2
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18
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0032486779
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For the use of chiral bicyclic 1,3-oxazolidines, see: (a) Review: Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503. (b) Leading reference to more recent work of A. I. Meyers et al.: Meyers, A. I.; Seefeld, M. A.; Lefker, B. A.; Blake, J. F.; Willard, P. G. J. Am. Chem. Soc. 1998, 120, 7429. (c) Review: Ager, D. J.; Prakash, I.; Schaad, D. Chem. Rev. 1996, 96, 835. (d) Leading reference to the work of H.-P. Husson et al.: François, D.; Lallemand, M.-C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. J. Org. Chem. 1997, 62, 8914.
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Meyers, A.I.1
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Willard, P.G.5
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19
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0038468227
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For the use of chiral bicyclic 1,3-oxazolidines, see: (a) Review: Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503. (b) Leading reference to more recent work of A. I. Meyers et al.: Meyers, A. I.; Seefeld, M. A.; Lefker, B. A.; Blake, J. F.; Willard, P. G. J. Am. Chem. Soc. 1998, 120, 7429. (c) Review: Ager, D. J.; Prakash, I.; Schaad, D. Chem. Rev. 1996, 96, 835. (d) Leading reference to the work of H.-P. Husson et al.: François, D.; Lallemand, M.-C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. J. Org. Chem. 1997, 62, 8914.
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Ager, D.J.1
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Schaad, D.3
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20
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0000735954
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For the use of chiral bicyclic 1,3-oxazolidines, see: (a) Review: Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503. (b) Leading reference to more recent work of A. I. Meyers et al.: Meyers, A. I.; Seefeld, M. A.; Lefker, B. A.; Blake, J. F.; Willard, P. G. J. Am. Chem. Soc. 1998, 120, 7429. (c) Review: Ager, D. J.; Prakash, I.; Schaad, D. Chem. Rev. 1996, 96, 835. (d) Leading reference to the work of H.-P. Husson et al.: François, D.; Lallemand, M.-C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. J. Org. Chem. 1997, 62, 8914.
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Lallemand, M.-C.2
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Tomas, A.4
Kunesch, N.5
Husson, H.-P.6
-
21
-
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0001088797
-
-
For related work with chiral 1,3-imidazolidines, see: (a) Alexakis, A.; Sedrani, R.; Normant, J. F.; Mangeney, P. Tetrahedron Asymmetry 1990, 1, 283. (b) Review: Alexakis, A.; Mangeney, P.; Jensen, N.; Tranchier, J.-P.; Gosmini, R.; Raussou, S. Pure Appl. Chem. 1996, 68, 531.
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Alexakis, A.1
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22
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0000967019
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For related work with chiral 1,3-imidazolidines, see: (a) Alexakis, A.; Sedrani, R.; Normant, J. F.; Mangeney, P. Tetrahedron Asymmetry 1990, 1, 283. (b) Review: Alexakis, A.; Mangeney, P.; Jensen, N.; Tranchier, J.-P.; Gosmini, R.; Raussou, S. Pure Appl. Chem. 1996, 68, 531.
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0026323731
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Hoppe, I.; Hoffmann, H.; Gärtner, I.; Krettek, T.; Hoppe, D. Synthesis 1991, 1157.
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Hoppe, I.1
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Hoppe, D.5
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25
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0025334189
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0001708808
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Bernardi, A.1
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Villa, R.5
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0026004928
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(d) Bernardi, A.; Cavicchioli, M.; Poli, G.; Scolastico, C.; Sidjimov, A. Tetrahedron 1991, 47, 7925.
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Bernardi, A.1
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0000145196
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Reviews: (a) Mukaiyama, T. Org. React. 1982, 28, 203. (b) Mukaiyama, T. Org. React. 1994, 46, 1. (c) Mukaiyama, T. Aldrichim. Acta 1996, 29, 59.
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Mukaiyama, T.1
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0002384398
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Reviews: (a) Mukaiyama, T. Org. React. 1982, 28, 203. (b) Mukaiyama, T. Org. React. 1994, 46, 1. (c) Mukaiyama, T. Aldrichim. Acta 1996, 29, 59.
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Mukaiyama, T.1
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0030445798
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Mukaiyama, T.1
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0000006503
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Wilkinson, R. G.; Shepherd, R. G.; Thomas, J. P.; Baughn, C. J. Am. Chem. Soc. 1961, 83, 2212.
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Wilkinson, R.G.1
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Baughn, C.4
-
34
-
-
1642607112
-
-
For a similiar result with appropriate lithium and cesium enolates, see Ref. 2f
-
For a similiar result with appropriate lithium and cesium enolates, see Ref. 2f.
-
-
-
-
36
-
-
1642607111
-
-
See Refs 7,8 for example
-
See Refs 7,8 for example.
-
-
-
-
37
-
-
0000803026
-
-
Cazeau, P.; Duboudin, F.; Moulines, F.; Babot, O.; Dunogues, J. Tetrahedron 1987, 43, 2075.
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Cazeau, P.1
Duboudin, F.2
Moulines, F.3
Babot, O.4
Dunogues, J.5
-
38
-
-
1642607114
-
-
Examples for Lewis acid-catalyzed epimerization, see Refs 7,8
-
Examples for Lewis acid-catalyzed epimerization, see Refs 7,8.
-
-
-
-
39
-
-
1642591545
-
-
note
-
-3, Flack parameter 0.00(2), hydrogens calculated and riding.
-
-
-
-
40
-
-
0003780608
-
-
Springer: Berlin Heidelberg
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(a) Review: Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer: Berlin Heidelberg 1986; pp 149-162. (b) Review: Weidmann, B.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1983, 22,37. (c) Review: Mahrwald, R. Chem. Rev. 1999, 99, 1095. (d) Reetz, M. T.; Peter, R. Tetrahedron Lett. 1981, 22, 4691.
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Reetz, M.T.1
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41
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84985510394
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(a) Review: Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer: Berlin Heidelberg 1986; pp 149-162. (b) Review: Weidmann, B.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1983, 22,37. (c) Review: Mahrwald, R. Chem. Rev. 1999, 99, 1095. (d) Reetz, M. T.; Peter, R. Tetrahedron Lett. 1981, 22, 4691.
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Weidmann, B.1
Seebach, D.2
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42
-
-
0001196589
-
-
(a) Review: Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer: Berlin Heidelberg 1986; pp 149-162. (b) Review: Weidmann, B.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1983, 22,37. (c) Review: Mahrwald, R. Chem. Rev. 1999, 99, 1095. (d) Reetz, M. T.; Peter, R. Tetrahedron Lett. 1981, 22, 4691.
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Mahrwald, R.1
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43
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0000217399
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(a) Review: Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer: Berlin Heidelberg 1986; pp 149-162. (b) Review: Weidmann, B.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1983, 22,37. (c) Review: Mahrwald, R. Chem. Rev. 1999, 99, 1095. (d) Reetz, M. T.; Peter, R. Tetrahedron Lett. 1981, 22, 4691.
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Reetz, M.T.1
Peter, R.2
-
44
-
-
1642607113
-
-
Note, that - compared to "ordinary" silyl enol ethers - the CIP-assignment is inverted due to the high priority of the oxazolidine residue
-
Note, that - compared to "ordinary" silyl enol ethers - the CIP-assignment is inverted due to the high priority of the oxazolidine residue.
-
-
-
-
45
-
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84987574236
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(a) Duthaler, R. O.; Herold, P.; Wyler-Helfer, S.; Riedicker, M. Helv. Chim. Acta 1990, 73, 659.
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Duthaler, R.O.1
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0027763603
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(b) Kanemasa, S.; Mori, T.; Tatsukawa, A. Tetrahedron Lett. 1993, 34, 8293.
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Kanemasa, S.1
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49
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84958315401
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(a) Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpí, F. J. Am. Chem. Soc. 1991, 113, 1047.
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Evans, D.A.1
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0033612353
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(b) Yoshida, Y.; Matsumoto, N.; Hamasaki, R.; Tanabe, Y. Tetrahedron Lett. 1999, 40, 4227.
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Yoshida, Y.1
Matsumoto, N.2
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Tanabe, Y.4
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51
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0033516536
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(c) Esteve, C.; Ferreró, M.; Romea, P.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1999, 40, 5083.
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Esteve, C.1
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33845551361
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Massad, S.K.1
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-
53
-
-
1642638198
-
-
The appropriate unlike diastereoisomers (2R,1′S or 2S,1′R) exhibit J = 8.0-9.0 Hz
-
The appropriate unlike diastereoisomers (2R,1′S or 2S,1′R) exhibit J = 8.0-9.0 Hz.
-
-
-
-
54
-
-
0000923042
-
-
(a) Felkin, H.; Cherest, M.; Prudent, N. Tetrahedron Lett. 1968, 18, 2199.
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Felkin, H.1
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0000906961
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(b) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 26, 3009.
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Kiyooka, S.1
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60
-
-
1642591544
-
-
note
-
-3, Flack parameter 0.04(2), hydrogens calculated and riding. Data sets were collected with an Enraf Nonius CAD4 diffractometer. Programs used: data reduction MoIEN, structure solution SHELXS-97, structure refinement SHELXL-97, graphics SCHAKAL-92. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CSD-138306 (anti-8d) and CSD-138307 (anti-11b). Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. Code +44(1223)336033, e-mail: deposit@ccdc.cam.ac.uk].
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-
-
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63
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84987486409
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For the synhesis of related triols see: (a) Seebach, D.; Lapierre, J.-M.; Jaworek, W.; Seiler, P. Helv. Chim. Acta 1993, 76, 459
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(1993)
Helv. Chim. Acta
, vol.76
, pp. 459
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Seebach, D.1
Lapierre, J.-M.2
Jaworek, W.3
Seiler, P.4
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65
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1642591095
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The enantiomeric series is formed from (S)-N-tosylamino alkanols, derived from naturally occuring amino acids; see Refs 7,8
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The enantiomeric series is formed from (S)-N-tosylamino alkanols, derived from naturally occuring amino acids; see Refs 7,8.
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